NPASS Compound

Structure

NPC28398 OpenBabel07101718242D 23 25 0 0 1 0 0 0 0 0999 V2000 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2812 0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7453 3.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 8 2 0 0 0 0 3 14 1 0 0 0 0 4 6 1 0 0 0 0 4 15 2 0 0 0 0 5 7 2 0 0 0 0 5 15 1 0 0 0 0 6 16 2 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 12 1 0 0 0 0 9 14 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 22 1 0 0 0 0 11 23 1 0 0 0 0 12 1 1 1 0 0 0 12 13 1 0 0 0 0 13 2 1 6 0 0 0 13 19 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 17 18 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.14
Volume:	328.216
LogP:	3.88
LogD:	3.778
LogS:	-4.42
# Rotatable Bonds:	5
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.853
Synthetic Accessibility Score:	2.945
Fsp3:	0.316
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.784
MDCK Permeability:	2.042903724941425e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.172

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.127
Plasma Protein Binding (PPB):	99.7146224975586%
Volume Distribution (VD):	0.682
Pgp-substrate:	1.470613718032837%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.206
CYP2C19-inhibitor:	0.976
CYP2C19-substrate:	0.163
CYP2C9-inhibitor:	0.934
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.98
CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.957
CYP3A4-substrate:	0.412

ADMET: Excretion

Clearance (CL):	14.882
Half-life (T1/2):	0.476

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.114
Drug-inuced Liver Injury (DILI):	0.843
AMES Toxicity:	0.14
Rat Oral Acute Toxicity:	0.241
Maximum Recommended Daily Dose:	0.06
Skin Sensitization:	0.223
Carcinogencity:	0.843
Eye Corrosion:	0.003
Eye Irritation:	0.37
Respiratory Toxicity:	0.086

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC28398

Natural Product ID:	NPC28398
*Common Name:**	(8S,8'r)-4-Hydroxy-3',4'-Methylenedioxy-7-Ona-8,8'-Ignan
IUPAC Name:	(2S,3R)-4-(1,3-benzodioxol-5-yl)-1-(4-hydroxyphenyl)-2,3-dimethylbutan-1-one
Synonyms:
Standard InCHIKey:	ADYNTRRRWKUCKH-OLZOCXBDSA-N
Standard InCHI:	InChI=1S/C19H20O4/c1-12(9-14-3-8-17-18(10-14)23-11-22-17)13(2)19(21)15-4-6-16(20)7-5-15/h3-8,10,12-13,20H,9,11H2,1-2H3/t12-,13+/m1/s1
SMILES:	C[C@H](Cc1ccc2c(c1)OCO2)[C@H](C)C(=O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL261195
PubChem CID:	44450606
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001969] Dibenzylbutane lignans

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO2754	Iryanthera lancifolia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579855]
NPO2754	Iryanthera lancifolia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18242997]
NPO2754	Iryanthera lancifolia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	MED	=	10.0	uM	PMID[538016]
NPT83	Cell Line	MCF7	Homo sapiens	Ratio	=	4.51	n.a.	PMID[538016]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	0.01	%	PMID[538016]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	50.1	%	PMID[538016]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC28398 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	1492
0.2-0.3	3654
0.3-0.4	9645
0.4-0.5	8737
0.5-0.6	3363
0.6-0.7	7747
0.7-0.8	7277
0.8-0.85	388
0.85-0.9	61
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9779	High Similarity	NPC46880
0.9149	High Similarity	NPC327052
0.9143	High Similarity	NPC86455
0.9143	High Similarity	NPC137920
0.9143	High Similarity	NPC125134
0.8963	High Similarity	NPC477694
0.8963	High Similarity	NPC477705
0.8963	High Similarity	NPC66905
0.8926	High Similarity	NPC474990
0.8904	High Similarity	NPC234152
0.8897	High Similarity	NPC477706
0.8881	High Similarity	NPC286683
0.8873	High Similarity	NPC229218
0.8873	High Similarity	NPC141817
0.8873	High Similarity	NPC192597
0.8873	High Similarity	NPC169214
0.8873	High Similarity	NPC176030
0.8836	High Similarity	NPC37220
0.8811	High Similarity	NPC46161
0.8811	High Similarity	NPC239608
0.8759	High Similarity	NPC88345
0.8759	High Similarity	NPC24257
0.8759	High Similarity	NPC153620
0.875	High Similarity	NPC304622
0.8741	High Similarity	NPC151167
0.8741	High Similarity	NPC5018
0.8741	High Similarity	NPC64948
0.8741	High Similarity	NPC123228
0.8741	High Similarity	NPC123722
0.8741	High Similarity	NPC276466
0.8732	High Similarity	NPC282291
0.8732	High Similarity	NPC166137
0.8722	High Similarity	NPC249788
0.8714	High Similarity	NPC90431
0.869	High Similarity	NPC30890
0.8671	High Similarity	NPC52664
0.8667	High Similarity	NPC179777
0.8667	High Similarity	NPC303680
0.8667	High Similarity	NPC90128
0.8667	High Similarity	NPC274356
0.8667	High Similarity	NPC84076
0.8658	High Similarity	NPC104728
0.8658	High Similarity	NPC35544
0.8643	High Similarity	NPC204592
0.8643	High Similarity	NPC88065
0.8643	High Similarity	NPC95485
0.8643	High Similarity	NPC89504
0.8603	High Similarity	NPC32163
0.8603	High Similarity	NPC16651
0.8593	High Similarity	NPC257589
0.8593	High Similarity	NPC53305
0.8592	High Similarity	NPC284409
0.8591	High Similarity	NPC267091
0.8591	High Similarity	NPC151425
0.8582	High Similarity	NPC474691
0.8571	High Similarity	NPC45404
0.8571	High Similarity	NPC300776
0.8571	High Similarity	NPC68779
0.8571	High Similarity	NPC5310
0.8571	High Similarity	NPC76687
0.8571	High Similarity	NPC176814
0.8571	High Similarity	NPC4982
0.8562	High Similarity	NPC472560
0.8562	High Similarity	NPC296575
0.8562	High Similarity	NPC239818
0.8562	High Similarity	NPC218471
0.8561	High Similarity	NPC239302
0.8552	High Similarity	NPC50954
0.8542	High Similarity	NPC104956
0.8533	High Similarity	NPC308555
0.8529	High Similarity	NPC92207
0.8529	High Similarity	NPC127937
0.8523	High Similarity	NPC243891
0.8516	High Similarity	NPC100425
0.8514	High Similarity	NPC474903
0.8506	High Similarity	NPC94155
0.85	High Similarity	NPC205915
0.85	High Similarity	NPC327410
0.8497	Intermediate Similarity	NPC68619
0.8497	Intermediate Similarity	NPC62518
0.8497	Intermediate Similarity	NPC215375
0.8493	Intermediate Similarity	NPC207732
0.8493	Intermediate Similarity	NPC229787
0.8487	Intermediate Similarity	NPC109765
0.8477	Intermediate Similarity	NPC25127
0.8467	Intermediate Similarity	NPC220577
0.8462	Intermediate Similarity	NPC475738
0.8451	Intermediate Similarity	NPC102260
0.8451	Intermediate Similarity	NPC230968
0.8444	Intermediate Similarity	NPC257976
0.8444	Intermediate Similarity	NPC164778
0.8444	Intermediate Similarity	NPC242372
0.8444	Intermediate Similarity	NPC4181
0.8435	Intermediate Similarity	NPC157133
0.8435	Intermediate Similarity	NPC189054
0.8435	Intermediate Similarity	NPC224687
0.8431	Intermediate Similarity	NPC167595
0.8431	Intermediate Similarity	NPC226759
0.8431	Intermediate Similarity	NPC202495
0.8429	Intermediate Similarity	NPC50763
0.8425	Intermediate Similarity	NPC119663
0.8421	Intermediate Similarity	NPC10205
0.8421	Intermediate Similarity	NPC344161
0.8421	Intermediate Similarity	NPC254163
0.8417	Intermediate Similarity	NPC172673
0.8417	Intermediate Similarity	NPC275950
0.8414	Intermediate Similarity	NPC110419
0.8411	Intermediate Similarity	NPC131121
0.8406	Intermediate Similarity	NPC226661
0.8403	Intermediate Similarity	NPC474784
0.8403	Intermediate Similarity	NPC470855
0.84	Intermediate Similarity	NPC62354
0.8397	Intermediate Similarity	NPC100420
0.8397	Intermediate Similarity	NPC475865
0.8394	Intermediate Similarity	NPC276014
0.8387	Intermediate Similarity	NPC295009
0.8387	Intermediate Similarity	NPC260640
0.8382	Intermediate Similarity	NPC30216
0.8382	Intermediate Similarity	NPC312404
0.8382	Intermediate Similarity	NPC273686
0.8378	Intermediate Similarity	NPC476336
0.837	Intermediate Similarity	NPC114298
0.837	Intermediate Similarity	NPC256167
0.8366	Intermediate Similarity	NPC261090
0.8366	Intermediate Similarity	NPC471405
0.8358	Intermediate Similarity	NPC225245
0.8357	Intermediate Similarity	NPC476345
0.8356	Intermediate Similarity	NPC312256
0.8356	Intermediate Similarity	NPC472564
0.8355	Intermediate Similarity	NPC287504
0.8345	Intermediate Similarity	NPC326065
0.8333	Intermediate Similarity	NPC470962
0.8333	Intermediate Similarity	NPC223807
0.8333	Intermediate Similarity	NPC205054
0.8333	Intermediate Similarity	NPC469512
0.8333	Intermediate Similarity	NPC177830
0.8333	Intermediate Similarity	NPC12854
0.8333	Intermediate Similarity	NPC469575
0.8333	Intermediate Similarity	NPC237441
0.8333	Intermediate Similarity	NPC261322
0.8323	Intermediate Similarity	NPC269906
0.8323	Intermediate Similarity	NPC225624
0.8323	Intermediate Similarity	NPC285973
0.8323	Intermediate Similarity	NPC474770
0.8322	Intermediate Similarity	NPC324929
0.8321	Intermediate Similarity	NPC120066
0.8313	Intermediate Similarity	NPC469506
0.8311	Intermediate Similarity	NPC73416
0.8311	Intermediate Similarity	NPC160777
0.831	Intermediate Similarity	NPC144662
0.831	Intermediate Similarity	NPC110958
0.831	Intermediate Similarity	NPC19890
0.8309	Intermediate Similarity	NPC163083
0.8309	Intermediate Similarity	NPC106659
0.8309	Intermediate Similarity	NPC160900
0.8309	Intermediate Similarity	NPC229084
0.8309	Intermediate Similarity	NPC18984
0.8301	Intermediate Similarity	NPC300757
0.8301	Intermediate Similarity	NPC180901
0.8299	Intermediate Similarity	NPC473090
0.8299	Intermediate Similarity	NPC254659
0.8298	Intermediate Similarity	NPC227002
0.8298	Intermediate Similarity	NPC106739
0.8298	Intermediate Similarity	NPC471505
0.8298	Intermediate Similarity	NPC153453
0.8298	Intermediate Similarity	NPC111888
0.8296	Intermediate Similarity	NPC80241
0.8296	Intermediate Similarity	NPC301641
0.8296	Intermediate Similarity	NPC201777
0.8289	Intermediate Similarity	NPC68882
0.8289	Intermediate Similarity	NPC157898
0.8289	Intermediate Similarity	NPC137813
0.8288	Intermediate Similarity	NPC472410
0.8286	Intermediate Similarity	NPC275724
0.8286	Intermediate Similarity	NPC181079
0.8286	Intermediate Similarity	NPC137427
0.8286	Intermediate Similarity	NPC285776
0.8286	Intermediate Similarity	NPC123196
0.8286	Intermediate Similarity	NPC319282
0.8286	Intermediate Similarity	NPC215941
0.8286	Intermediate Similarity	NPC65935
0.8286	Intermediate Similarity	NPC244246
0.8286	Intermediate Similarity	NPC173308
0.8286	Intermediate Similarity	NPC311419
0.828	Intermediate Similarity	NPC469475
0.828	Intermediate Similarity	NPC469518
0.8278	Intermediate Similarity	NPC32079
0.8278	Intermediate Similarity	NPC295977
0.8278	Intermediate Similarity	NPC58310
0.8278	Intermediate Similarity	NPC472279
0.8278	Intermediate Similarity	NPC477700
0.8269	Intermediate Similarity	NPC99968
0.8267	Intermediate Similarity	NPC55327
0.8267	Intermediate Similarity	NPC145569
0.8267	Intermediate Similarity	NPC216223
0.8267	Intermediate Similarity	NPC127827
0.8264	Intermediate Similarity	NPC52968
0.8264	Intermediate Similarity	NPC231719
0.8261	Intermediate Similarity	NPC213711
0.8261	Intermediate Similarity	NPC40352

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC28398 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	929
0.2-0.3	1396
0.3-0.4	2524
0.4-0.5	2065
0.5-0.6	1207
0.6-0.7	586
0.7-0.8	141
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD6143	Clinical (unspecified phase)
0.8571	High Similarity	NPD6980	Clinical (unspecified phase)
0.8309	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD7458	Discontinued
0.8201	Intermediate Similarity	NPD9494	Approved
0.8158	Intermediate Similarity	NPD7028	Phase 2
0.8125	Intermediate Similarity	NPD3818	Discontinued
0.806	Intermediate Similarity	NPD5536	Phase 2
0.8013	Intermediate Similarity	NPD3882	Suspended
0.8	Intermediate Similarity	NPD2798	Approved
0.7971	Intermediate Similarity	NPD3972	Approved
0.7919	Intermediate Similarity	NPD4628	Phase 3
0.7895	Intermediate Similarity	NPD5283	Phase 1
0.7891	Intermediate Similarity	NPD2935	Discontinued
0.7857	Intermediate Similarity	NPD1876	Approved
0.7838	Intermediate Similarity	NPD2344	Approved
0.7821	Intermediate Similarity	NPD1934	Approved
0.7821	Intermediate Similarity	NPD37	Approved
0.7818	Intermediate Similarity	NPD7685	Pre-registration
0.7805	Intermediate Similarity	NPD7074	Phase 3
0.7771	Intermediate Similarity	NPD2801	Approved
0.7744	Intermediate Similarity	NPD7054	Approved
0.7738	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7473	Discontinued
0.7703	Intermediate Similarity	NPD2799	Discontinued
0.7702	Intermediate Similarity	NPD7199	Phase 2
0.7697	Intermediate Similarity	NPD7472	Approved
0.7688	Intermediate Similarity	NPD6234	Discontinued
0.7682	Intermediate Similarity	NPD4110	Phase 3
0.7682	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD1357	Approved
0.7673	Intermediate Similarity	NPD4966	Approved
0.7673	Intermediate Similarity	NPD4967	Phase 2
0.7673	Intermediate Similarity	NPD4965	Approved
0.7671	Intermediate Similarity	NPD1240	Approved
0.7658	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6232	Discontinued
0.764	Intermediate Similarity	NPD5494	Approved
0.7632	Intermediate Similarity	NPD2309	Approved
0.7625	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1933	Approved
0.7616	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD5978	Approved
0.761	Intermediate Similarity	NPD5977	Approved
0.7607	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD1283	Approved
0.7589	Intermediate Similarity	NPD1608	Approved
0.7584	Intermediate Similarity	NPD1510	Phase 2
0.7568	Intermediate Similarity	NPD1607	Approved
0.7562	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7808	Phase 3
0.7545	Intermediate Similarity	NPD6797	Phase 2
0.7534	Intermediate Similarity	NPD3764	Approved
0.7532	Intermediate Similarity	NPD6873	Phase 2
0.7532	Intermediate Similarity	NPD1511	Approved
0.7518	Intermediate Similarity	NPD3705	Approved
0.75	Intermediate Similarity	NPD6355	Discontinued
0.75	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD7251	Discontinued
0.75	Intermediate Similarity	NPD447	Suspended
0.7481	Intermediate Similarity	NPD228	Approved
0.7456	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6166	Phase 2
0.7455	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7003	Approved
0.7451	Intermediate Similarity	NPD8166	Discontinued
0.7436	Intermediate Similarity	NPD6273	Approved
0.7436	Intermediate Similarity	NPD1512	Approved
0.7434	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD943	Approved
0.7429	Intermediate Similarity	NPD1651	Approved
0.7425	Intermediate Similarity	NPD5844	Phase 1
0.7421	Intermediate Similarity	NPD6386	Approved
0.7421	Intermediate Similarity	NPD6385	Approved
0.7415	Intermediate Similarity	NPD3268	Approved
0.7403	Intermediate Similarity	NPD2354	Approved
0.7399	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6559	Discontinued
0.7394	Intermediate Similarity	NPD3926	Phase 2
0.7394	Intermediate Similarity	NPD1281	Approved
0.7383	Intermediate Similarity	NPD230	Phase 1
0.7376	Intermediate Similarity	NPD17	Approved
0.7372	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7228	Approved
0.7358	Intermediate Similarity	NPD4380	Phase 2
0.7357	Intermediate Similarity	NPD9545	Approved
0.7347	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3027	Phase 3
0.7338	Intermediate Similarity	NPD3750	Approved
0.7333	Intermediate Similarity	NPD3021	Approved
0.7333	Intermediate Similarity	NPD3022	Approved
0.7329	Intermediate Similarity	NPD1465	Phase 2
0.7329	Intermediate Similarity	NPD7819	Suspended
0.732	Intermediate Similarity	NPD1549	Phase 2
0.7315	Intermediate Similarity	NPD4060	Phase 1
0.731	Intermediate Similarity	NPD2797	Approved
0.7308	Intermediate Similarity	NPD6799	Approved
0.7301	Intermediate Similarity	NPD7075	Discontinued
0.7296	Intermediate Similarity	NPD3455	Phase 2
0.729	Intermediate Similarity	NPD3887	Approved
0.7256	Intermediate Similarity	NPD919	Approved
0.7255	Intermediate Similarity	NPD2353	Approved
0.7255	Intermediate Similarity	NPD7266	Discontinued
0.7255	Intermediate Similarity	NPD2346	Discontinued
0.7255	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6599	Discontinued
0.7246	Intermediate Similarity	NPD1241	Discontinued
0.723	Intermediate Similarity	NPD7095	Approved
0.7226	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD3847	Discontinued
0.72	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3620	Phase 2
0.72	Intermediate Similarity	NPD2979	Phase 3
0.7192	Intermediate Similarity	NPD1203	Approved
0.719	Intermediate Similarity	NPD2796	Approved
0.719	Intermediate Similarity	NPD2438	Suspended
0.7188	Intermediate Similarity	NPD824	Approved
0.7186	Intermediate Similarity	NPD5242	Approved
0.7181	Intermediate Similarity	NPD2313	Discontinued
0.7181	Intermediate Similarity	NPD6798	Discontinued
0.7179	Intermediate Similarity	NPD6190	Approved
0.7178	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2821	Approved
0.7169	Intermediate Similarity	NPD8127	Discontinued
0.7152	Intermediate Similarity	NPD2534	Approved
0.7152	Intermediate Similarity	NPD2532	Approved
0.7152	Intermediate Similarity	NPD2533	Approved
0.7152	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1471	Phase 3
0.7135	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3019	Approved
0.7133	Intermediate Similarity	NPD2932	Approved
0.7133	Intermediate Similarity	NPD4626	Approved
0.7124	Intermediate Similarity	NPD4308	Phase 3
0.7105	Intermediate Similarity	NPD2492	Phase 1
0.7103	Intermediate Similarity	NPD1481	Phase 2
0.7099	Intermediate Similarity	NPD7411	Suspended
0.7091	Intermediate Similarity	NPD3749	Approved
0.7089	Intermediate Similarity	NPD4357	Discontinued
0.7081	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3226	Approved
0.7075	Intermediate Similarity	NPD3267	Approved
0.7075	Intermediate Similarity	NPD3266	Approved
0.7073	Intermediate Similarity	NPD2296	Approved
0.7069	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1247	Approved
0.7063	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7577	Discontinued
0.7055	Intermediate Similarity	NPD6801	Discontinued
0.7047	Intermediate Similarity	NPD6832	Phase 2
0.7044	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6876	Approved
0.7037	Intermediate Similarity	NPD6875	Approved
0.7034	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1535	Discovery
0.7022	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD8032	Phase 2
0.702	Intermediate Similarity	NPD6233	Phase 2
0.702	Intermediate Similarity	NPD4062	Phase 3
0.7013	Intermediate Similarity	NPD3748	Approved
0.7011	Intermediate Similarity	NPD7280	Phase 3
0.7011	Intermediate Similarity	NPD8313	Approved
0.7011	Intermediate Similarity	NPD8312	Approved
0.7011	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7281	Phase 3
0.7	Intermediate Similarity	NPD5049	Phase 3
0.6994	Remote Similarity	NPD7240	Approved
0.6994	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7110	Phase 1
0.6993	Remote Similarity	NPD1894	Discontinued
0.6987	Remote Similarity	NPD5958	Discontinued
0.6986	Remote Similarity	NPD9717	Approved
0.6986	Remote Similarity	NPD9269	Phase 2
0.6974	Remote Similarity	NPD3140	Approved
0.6974	Remote Similarity	NPD3142	Approved
0.6972	Remote Similarity	NPD9493	Approved
0.697	Remote Similarity	NPD5353	Approved
0.6968	Remote Similarity	NPD6100	Approved
0.6968	Remote Similarity	NPD2531	Phase 2
0.6968	Remote Similarity	NPD6099	Approved
0.6962	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1470	Approved
0.6954	Remote Similarity	NPD5110	Phase 2
0.6954	Remote Similarity	NPD5111	Phase 2
0.6954	Remote Similarity	NPD5109	Approved
0.6944	Remote Similarity	NPD5585	Approved
0.6944	Remote Similarity	NPD9268	Approved
0.6943	Remote Similarity	NPD2800	Approved
0.6941	Remote Similarity	NPD7852	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data